Tetrahydrofuran → HCID 19895465, compound

HRID 892468Notes

Reaction equation

HRID 892468 reaction equation
[BH4-].[Na+].[C:3]([C:5]1[C:6]([N+:13]([O-:15])=[O:14])=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=[O:9])#[N:4].O1CCCC1>C(O)C>[OH:9][CH2:8][C:7]1[C:6]([N+:13]([O-:15])=[O:14])=[C:5]([CH:12]=[CH:11][CH:10]=1)[C:3]#[N:4]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 19895505HCID 19895505, compound

Product 1

HCID 19895465HCID 19895465, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of NaBH4 (0.2 g) in ethanol (10 ml) at ice bath temperature was added a solution of 3-cyano-2-nitrobenzaldehyde from Example 2c (0.93 g) in ethanol:tetrahydrofuran (15 ml:15 ml). After the addition was completed, the solution was warmed to ambient temperature and stirred for 30 minutes. The volatiles were removed under aspirator vacuum and the residue suspended in water. Dilute (1% aqueous) hydrochloric acid was added slowly until gas evolution had ceased. Ethyl acetate was then added followed by saturation of the aqueous layer with K2CO3. The layers were separated and the ethyl acetate layer was washed with brine, dried (Na2SO4) and concentrated to leave the title product (0.85 g, 90%) as a yellow solid: tlc, Rf =0.25, silica gel, ethyl acetate:hexane (1:1).

Workup

  1. additionAfter the addition
  2. customThe volatiles were removed under aspirator vacuum
  3. additionDilute (1% aqueous) hydrochloric acid
  4. additionwas added slowly until gas evolution
  5. additionEthyl acetate was then added
  6. customThe layers were separated
  7. washthe ethyl acetate layer was washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-93cedaff843b4fc98930b925303a6b38
Source dataset
uspto-grants-1992_06
Patent number
US05118688

Reaction notes

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